BUILDING YOUR BENCH: A PRACTICAL GUIDE TO CULTIVATING VC RELATIONSHIPS FOR HEALTH TECH ANGEL SYNDICATES
DISCLAIMER
The thoughts and opinions expressed in this essay are my own and do not reflect those of my employer.
ABSTRACT
Angel investors in healthcare technology face a unique challenge in building relationships with institutional venture capital firms. Unlike consumer tech where product-market fit can be demonstrated quickly through user growth metrics, health tech requires deep domain expertise, longer sales cycles, and complex regulatory understanding that makes VC partnership particularly valuable. This essay provides a tactical framework for angel investors and syndicates to systematically build a network of trusted VC relationships for deal syndication. Key topics include:
- Why healthcare angels need VC relationships more than other sectors
- Practical strategies for initial outreach and relationship building
- How to add value to VCs before asking for anything in return
- Deal flow sharing mechanics and reciprocity dynamics
- Red flags in VC partnerships and when to walk away
- Structuring syndicate deals with institutional lead investors
- Long-term relationship maintenance and network effects
The essay draws on real-world examples and provides actionable frameworks for both first-time angels and established syndicates looking to strengthen their institutional relationships.
TABLE OF CONTENTS
Introduction: Why Health Tech Angels Need VC Friends
The Structural Advantage of VC Partnerships in Healthcare
Getting Your Foot in the Door Without Looking Desperate
The Value Exchange: What Angels Actually Offer VCs
Deal Flow Sharing Mechanics and Unwritten Rules
Structuring Syndicate Rounds with Institutional Leads
Red Flags and When to Cut Ties
Playing the Long Game: Relationship Maintenance
Conclusion: Building Durable Networks in an Opaque Market
INTRODUCTION: WHY HEALTH TECH ANGELS NEED VC FRIENDS
Most advice about angel investing treats venture capital firms like distant cousins you only see at weddings, occasionally useful but mostly operating in their own world. That might work fine if you are writing checks into consumer apps or developer tools where the path to product-market fit is relatively straightforward and exits happen in five to seven years. Healthcare is not that. Healthcare is a byzantine nightmare of regulatory complexity, eighteen-month sales cycles, and incumbents with moats so deep they make medieval castles look accessible. Which means that as a health tech angel, having strong relationships with institutional VCs is not just nice to have, it is basically table stakes if you want to build a portfolio that actually returns capital.
The reason is pretty simple when you think about it. Healthcare companies take longer to mature than almost any other sector. A digital health company that raises a seed round today might not have meaningful revenue traction for two years, might not hit series A milestones for three or four years, and might not exit for eight to twelve years assuming everything goes well. Compare that to a B2B SaaS company where you can demonstrate product-market fit in twelve months and scale to series B in three years. The longer time horizons in healthcare mean that angels need downstream capital partners who understand the sector, have the patience for extended development cycles, and can write the larger checks required to get these companies to escape velocity.
But it goes deeper than just needing follow-on capital. Healthcare VCs have networks that angels simply cannot replicate on their own. They have relationships with health system innovation teams, connections to pharma corporate development groups, intros to CMS officials who can navigate reimbursement strategy, and pattern recognition from seeing hundreds of healthcare pitches a year. When you syndicate a deal with a strong healthcare VC, you are not just getting their money, you are getting their entire platform and everything that comes with it. That leverage is worth way more than the check size would suggest.
The challenge is that most angels have no idea how to build these relationships systematically. They might know a couple of VCs from their MBA program or from working at a tech company, but those relationships tend to be shallow and transactional. When deal flow shows up, they send a cold email saying hey do you want to look at this and wonder why they never hear back. Or worse, they treat VCs like some kind of mysterious priesthood where the only way in is through warm introductions and secret handshakes. The reality is that building a strong bench of VC relationships is totally doable if you approach it with the same rigor you would bring to sourcing deals or conducting diligence. It just requires understanding what VCs actually want, being useful before you ask for anything, and playing a long game that compounds over multiple years.
THE STRUCTURAL ADVANTAGE OF VC PARTNERSHIPS IN HEALTHCARE
Before getting into tactics, it helps to understand why healthcare angels benefit more from VC relationships than angels in other sectors. Consumer tech angels can often build successful portfolios by focusing on product sense and go-to-market execution. Enterprise software angels can lean on their experience selling to CTOs and understanding unit economics. Healthcare angels need all of that plus domain expertise in clinical workflows, regulatory strategy, reimbursement models, and incumbent competitive dynamics. That is a much heavier lift and frankly most angels do not have all those skills in-house.
Healthcare VCs on the other hand have built entire investment platforms around this expertise. Firms like Andreessen Horowitz Bio plus Health, Transformation Capital, Oak HC slash FT, and Optum Ventures have teams that include former healthcare operators, clinical advisors, regulatory experts, and business development professionals who spend all day thinking about these problems. When you co-invest with them, you get access to that infrastructure. Your portfolio company that is trying to navigate FDA breakthrough device designation suddenly has connections to regulatory consultants who have done it twenty times before. Your company trying to sell into health systems gets intros to innovation leaders at major IDNs. Your company building AI for prior authorization gets advice on how to structure a risk-sharing agreement that payers will actually sign.
The other structural advantage is pattern recognition. Healthcare VCs see deal flow at scale in a way that even the most active angels cannot match. A firm like General Catalyst or NEA might look at three hundred healthcare companies a year across their entire investment team. They know which business models are working, which regulatory pathways are getting easier, which incumbents are actually acquirable versus just saying they want to do deals. That pattern recognition helps them pick winners but it also helps them support portfolio companies more effectively because they have seen the movie before.
The third advantage is signaling value. Like it or not, healthcare is a sector where institutional validation matters more than in other parts of tech. When a respected healthcare VC leads your series A, it signals to customers, future investors, and acquirers that smart money believes in what you are building. Health systems are notoriously risk-averse and often will not take a meeting with an early-stage startup unless they see a recognizable VC name on the cap table. That signaling value compounds over time and can be the difference between getting enterprise contracts versus being stuck in pilot purgatory.
All of this means that if you are serious about building a healthcare angel portfolio, cultivating relationships with institutional VCs should be one of your top priorities. Not just for the current fund but as an ongoing part of your investment practice. The question is how to actually do it in a way that does not feel gross or transactional.
GETTING YOUR FOOT IN THE DOOR WITHOUT LOOKING DESPERATE
Cold outreach to VCs is mostly a waste of time but not for the reasons people think. The issue is not that VCs are too busy or too important to respond to strangers. The issue is that most cold outreach provides zero value to the recipient and makes it obvious you want something without being willing to give anything first. If your first interaction with a VC is forwarding them a deck and asking if they want to invest, you have already lost. They get fifty of those emails a day and ignore basically all of them unless the company is super hot or came through a trusted referral.
The right way to start is by being genuinely helpful before you ask for anything. This sounds obvious but most people skip this step because they are impatient or do not know what helpful actually looks like to a VC. Here is what actually works. Find a VC whose portfolio and thesis you respect, ideally someone focused on healthcare or at least adjacent to it. Read everything they have written, understand their investment focus, and look at their recent investments to get a sense of what they care about. Then find ways to be useful without expecting anything in return.
One tactic that works surprisingly well is sharing deal flow before you invest yourself. If you see an interesting healthcare company that fits a VC’s thesis but you have not committed yet, send a short note saying hey I am looking at this company in remote patient monitoring, noticed you invested in X and Y which are adjacent, thought you might want to look too. No ask, no expectation, just sharing information. If the deal is good and the VC takes a meeting, you have done them a favor. If they pass but appreciate you thinking of them, you have still built goodwill. Either way you are on their radar as someone who sees interesting deal flow.
Another approach is to offer domain expertise if you have it. Let’s say you spent ten years working in revenue cycle management at health systems and you see a VC who just invested in an RCM-adjacent company. Send them a note saying congrats on the investment, I worked in this space for a decade, happy to provide customer intros or answer questions about how these systems actually work. No one turns down free expertise especially in healthcare where domain knowledge is so valuable. You help them support their portfolio company, they remember you exist, and you start building a relationship based on actually being useful rather than just wanting something.
The third tactic is creating content that showcases your thinking. If you are writing detailed analyses of healthcare markets, regulatory trends, or company deep dives, VCs will read that stuff because it helps them do their jobs better. Tag them when you write something relevant to their portfolio or thesis, not in an annoying way but as a genuine hey thought you might find this interesting given your focus on X. The best VCs are intellectually curious and love finding people who think deeply about the same problems they do. If your writing demonstrates real insight, they will want to stay connected because you might be a useful sounding board in the future.
The key to all of this is patience and not being transactional. You are not trying to get a meeting next week. You are trying to become someone this VC knows, respects, and thinks of when opportunities arise. That takes months not days. But if you consistently provide value, share interesting deal flow, and demonstrate deep thinking about healthcare markets, you will naturally end up in conversations. And once you are in conversations, you can start talking about co-investing on deals where it makes sense.
THE VALUE EXCHANGE: WHAT ANGELS ACTUALLY OFFER VCS
Most angels underestimate what they bring to the table in VC relationships because they focus too much on check size. Yes, institutional VCs write bigger checks and have more resources. But angels have things VCs desperately need and often cannot get any other way. Understanding this value exchange is critical because if you do not know what you offer, you cannot position yourself effectively.
The first thing angels offer is optionality on deal access. VCs have to be selective about what they spend time on because their model requires concentrated bets and active portfolio support. But they also hate missing deals that could have been great. Angels solve this by taking first meetings with companies that are too early or too small for institutional capital but might be interesting in twelve months. You become their eyes and ears on the earliest stage opportunities, helping them track companies before they formally raise series A. When one of those companies starts showing real traction, you can bring the VC in at exactly the right moment.
The second thing angels offer is domain expertise that VCs do not have in-house. Even the best healthcare VCs cannot be experts in every subsector. If you have deep expertise in lab operations, ophthalmology practice management, behavioral health billing, or any of a hundred other healthcare niches, that knowledge is incredibly valuable to VCs who are looking at deals in those spaces. They might have general healthcare expertise but you have the specific operational knowledge that helps them underwrite risks and spot red flags. That makes you a useful diligence partner even on deals you did not source.
The third thing angels offer is speed and flexibility. VCs have investment committees, partnership dynamics, fund mandates, and all kinds of process that slows them down. Angels can move fast, write small checks into rounds that do not quite fit VC mandates, and take risks on non-consensus opportunities. This is especially valuable in pre-seed and seed rounds where founders want to close quickly and do not want to spend months in diligence. If a VC likes a company but cannot lead the round for whatever reason, having trusted angels who can fill out the cap table makes the deal possible.
The fourth thing angels offer is access to founder networks. Good angels know lots of entrepreneurs, either from their operating careers, previous investments, or just being plugged into the ecosystem. VCs are always looking for deal flow and referrals from trusted sources are the best kind. If you consistently introduce them to interesting founders or help them source deals through your network, you become an important part of their deal flow engine. That relationship becomes self-reinforcing because the more they invest, the more they want to keep you plugged in.
The key is to be explicit about this value exchange, not in a weird transactional way but just in terms of understanding what you bring. When you reach out to a VC about a potential co-investment, you should be able to articulate why it makes sense for both sides. Maybe you are bringing domain expertise they need. Maybe you are providing optionality on a company they want to track but cannot invest in yet. Maybe you are solving a timing problem where the founder wants to close before the VC can finish diligence. Whatever it is, be clear about the value exchange so everyone understands what they are getting from the relationship.
DEAL FLOW SHARING MECHANICS AND UNWRITTEN RULES
Once you have built initial relationships with a few VCs, the next step is figuring out how to actually collaborate on deals. This is where things get tricky because there are all kinds of unwritten rules and norms that govern how deal flow sharing works. Get these wrong and you can burn bridges pretty quickly. Get them right and you build durable relationships that compound over time.
The first rule is to always be transparent about your involvement. If you are already invested in a company and you are bringing a VC in for follow-on funding, say that upfront. If you are just passing along deal flow without having committed yourself, say that too. VCs hate surprises and they definitely hate feeling like you are using them for due diligence while planning to invest yourself regardless of what they think. Transparency builds trust and trust is the foundation of everything in these relationships.
The second rule is to respect lead dynamics. If a VC is leading a round, they get to set terms, control board seats, and generally run the process. As an angel or syndicate, you are filling out the round not negotiating deal structure. This means you should be flexible on terms, responsive to diligence requests, and generally make life easy for the lead investor. The worst thing you can do is slow down a round or create complexity that makes the lead’s job harder. If you cannot play a supporting role, do not join the syndicate.
The third rule is reciprocity matters a lot. If a VC consistently shares deal flow with you or invites you into their deals, you should return the favor when you see opportunities that fit their mandate. This does not mean sharing every deal you see but it does mean thinking about them when something relevant crosses your desk. Relationships that are one-sided do not last long. The best angel-VC relationships have a natural give and take where both sides are constantly looking for ways to help each other.
The fourth rule is to be selective about what you share. Quality matters way more than quantity. If you forward every mediocre deal that comes across your desk, you train VCs to ignore you because you have no filter. But if you only share the best opportunities you see, even if it is just two or three deals a year, VCs will pay attention because they know you have good judgment. Think of it like a reputation system where every deal you share either builds or degrades your credibility.
The fifth rule is to be helpful in diligence even when you are not investing. Sometimes a VC will ask for your input on a deal that does not quite work for you but fits their mandate. Maybe it is outside your check size range or you have concerns about the founder but the market is interesting. You should still help with diligence if you can, providing whatever insights or connections you have. This costs you time but it deepens the relationship because you are demonstrating that you care about their success not just your own deals.
The sixth rule is to never shop deals around as a negotiating tactic. If you tell a VC you are excited about a company and want to work together, do not then go talk to three other VCs trying to create a bidding war. That kind of behavior gets you blacklisted fast. If you want to run a formal process for a company you are helping fundraise, that is fine, but be upfront about it. Do not pretend you are in exclusive discussions while simultaneously talking to everyone else.
The unwritten meta-rule underneath all of this is that reputation compounds faster in VC circles than almost anywhere else. VCs talk to each other constantly, they compare notes on deals, and they definitely compare notes on angel investors and syndicate leads. If you build a reputation for being reliable, transparent, and helpful, that opens doors everywhere. If you build a reputation for being difficult, slow, or playing games, you will find yourself shut out of opportunities pretty quickly. This is especially true in healthcare where the VC community is smaller and more interconnected than in other sectors.
STRUCTURING SYNDICATE ROUNDS WITH INSTITUTIONAL LEADS
The mechanics of actually syndicating a deal with institutional VCs requires understanding how they think about round construction and what terms they care about. This is different from angel-to-angel syndication where everyone is mostly just following a lead investor without much negotiation. When institutional capital is involved, there are more moving parts and more potential friction points.
The most common structure is a VC-led round where the institution sets the terms, takes a board seat, and writes the largest check. Angels then fill out the round alongside the VC, typically on the same terms or occasionally on slightly different terms if they are coming in through a side vehicle. As an angel or syndicate, your job in this structure is to make the lead’s life as easy as possible. This means being responsive to diligence requests, signing documents quickly, and generally not creating process overhead. The faster and smoother you make the process, the more likely the VC will want to work with you again in the future.
One nuance that matters is pro rata rights. VCs almost always negotiate for pro rata or super pro rata rights to participate in future rounds. As an angel, you probably will not get pro rata unless you are writing a meaningfully large check or bringing some other strategic value. This is fine and expected. But you should understand the implications for your ownership trajectory. If you invest at seed and do not have pro rata, you will get diluted in series A and series B which means your ultimate returns depend heavily on getting in early enough that even with dilution you still make good money on an exit. This is why syndicate economics often make sense because you can write a slightly larger check as a group and sometimes negotiate better terms than you would individually.
Another consideration is side letters and special terms. Sometimes angels or syndicates will negotiate for specific rights like information access, advisory relationships, or observer seats that are separate from the main term sheet. This can work but you have to be careful not to create a precedent that complicates future rounds. VCs generally dislike complex cap tables with lots of side agreements because it makes their job harder when raising follow-on rounds. If you are going to ask for special terms, make sure they are actually valuable to you and not just something you are doing because you can.
The information rights question is particularly important in healthcare because these companies take so long to mature. If you are investing at seed and the company does not exit for ten years, you want to make sure you are getting regular updates on progress, financials, and strategic direction. Most seed-stage investments do not come with formal information rights but you can often negotiate for informal updates or inclusion in investor communication lists. This matters because staying close to portfolio companies helps you pattern match across your portfolio and also gives you opportunities to provide help when companies hit roadblocks.
Board observer seats are another area where angels sometimes negotiate but should probably not. Board observers create process overhead for companies and VCs without giving you any real governance power. Unless you are writing a very large check or bringing some unique strategic value, you are better off building a strong relationship with the company and getting informal access rather than formalizing it through a board observer role. The exception is if you are running a large syndicate and need formal information rights to satisfy your LPs, in which case a board observer seat might make sense.
The most important thing in all of this is to make yourself easy to work with. VCs have lots of options for filling out their rounds and they will naturally gravitate toward angels and syndicates that do not create friction. This means having standard documents ready, being responsive on Slack or email, and generally treating the fundraising process as a professional transaction rather than a social exercise. The easier you make their lives, the more deals you will get invited into.
RED FLAGS AND WHEN TO WALK AWAY
Not all VC relationships are worth building and knowing when to walk away is just as important as knowing how to cultivate good relationships. There are some pretty clear red flags that indicate a VC is not going to be a good long-term partner and recognizing these early can save you a lot of wasted time and frustration.
The first red flag is if a VC consistently shops your deal flow without investing. Some VCs will use angel relationships as a free due diligence service, taking meetings with companies you introduce but never actually writing checks. They are basically outsourcing their sourcing work to you without providing any reciprocal value. This is fine once or twice but if it becomes a pattern, you should stop sharing deals with them. Your deal flow has value and you should only share it with people who will actually act on it.
The second red flag is bad behavior toward founders. If you see a VC treating entrepreneurs poorly, being disrespectful in meetings, or slow-rolling diligence for no good reason, that is a sign you do not want to be associated with them. Your reputation in the founder community matters and co-investing with VCs who have bad reputations will damage your brand. Pay attention to how VCs treat companies that they pass on. Do they provide thoughtful feedback or just ghost? Do they stay connected to interesting founders even when the timing is not right for investment? The best VCs maintain relationships even with companies they do not invest in because they understand it is a long-term relationship business.
The third red flag is misalignment on company-building philosophy. Some VCs are hyper-aggressive about growth at all costs, pushing companies to hire fast and spend big even when unit economics do not support it. Other VCs are too conservative, encouraging founders to stay small and scrappy long after the company needs to scale. If you have strong views on how healthcare companies should be built and a VC’s portfolio consistently reflects a different philosophy, you are probably not going to work well together. This does not mean they are wrong, just that the relationship is unlikely to be productive.
The fourth red flag is lack of reciprocity. If you are consistently sharing deal flow, making introductions, and helping with diligence but never getting invited into any of their deals, that is a one-sided relationship that is not worth maintaining. Good VC relationships have natural give and take. If you are always giving and never getting anything back, you should redirect your energy to relationships that are more balanced.
The fifth red flag is playing games with valuations or terms. Some VCs will agree to terms with a founder and then try to renegotiate at the last minute, hoping the founder is desperate enough to accept worse terms rather than restart the fundraising process. This is brutal and unfair to founders and if you see a VC doing this, you should probably not work with them. Integrity matters a lot in venture and VCs who do not honor their commitments are not worth being associated with.
The hardest part about walking away from VC relationships is that the industry is small and you never want to burn bridges unnecessarily. But there is a difference between burning bridges and just deciding to invest your time elsewhere. You can politely stop engaging with a VC without making it a dramatic breakup. Just start responding less frequently to their emails, stop sharing deal flow, and redirect your energy to relationships that are more productive. Most people will get the hint and everyone moves on without hard feelings.
PLAYING THE LONG GAME: RELATIONSHIP MAINTENANCE
Building initial relationships with VCs is the easy part. The hard part is maintaining those relationships over multiple years so they deepen into real partnerships rather than fading away. This requires intentional effort and treating relationship maintenance as a core part of your investment practice.
The simplest thing you can do is stay in regular touch even when you are not actively working on deals together. This does not mean annoying people with unnecessary emails but it does mean reaching out every few months with something genuinely useful. Maybe you saw an article that relates to their portfolio or their investment thesis. Maybe you met a founder who would be interesting for them to know even if there is no immediate deal opportunity. Maybe you just want to grab coffee and compare notes on what you are seeing in the market. The key is staying top of mind without being intrusive.
Another tactic is to help their portfolio companies when you can. If a VC you work with has a portfolio company that could benefit from an intro to someone in your network, make that introduction proactively. If you see a job posting from one of their companies, share it with relevant people you know. These small gestures cost you almost nothing but they build goodwill and demonstrate that you care about their success not just your own deals. Over time this kind of behavior cements relationships because you become a real partner rather than just someone who shows up when you want something.
The third tactic is to include them in your content distribution if you are writing or creating thought leadership. Most VCs are intellectually curious and love reading good content about healthcare markets, trends, and companies. If you are regularly publishing analysis, make sure you are sharing it with your VC relationships. This keeps you on their radar and also gives them a reason to engage with you since they can respond to your content with their own thoughts or questions.
The fourth tactic is to build relationships with multiple people at the same firm. Most VC funds have several partners plus associates and principals who are often the first point of contact for new deals. Do not just focus on the most senior partner. Build relationships across the investment team because those junior people will be senior partners eventually and they often have more time to engage with angel networks than the partners do. Plus different people at the same firm will have different areas of focus and relationships with multiple team members gives you more surface area for collaboration.
The fifth tactic is to host events or dinners that bring VCs together with founders and other angels. The healthcare investing community is relatively small and people genuinely enjoy getting together to compare notes and meet new people. If you can host thoughtful events that provide real value rather than just being networking cattle calls, you become a hub in the network rather than just a node. This gives you outsized influence and access because everyone wants to be connected to people who bring the community together.
The meta-point here is that relationship maintenance compounds over time in ways that are hard to see in the moment. A casual coffee this month might lead to a co-investment in six months which leads to an introduction to another VC in a year which leads to you getting invited into a hot deal two years from now. The chains of causation are long and unpredictable which means you have to play a patient game and trust that investing in relationships will pay off even if you cannot trace the exact return path.
CONCLUSION: BUILDING DURABLE NETWORKS IN AN OPAQUE MARKET
Healthcare venture capital remains stubbornly opaque compared to other sectors. Information does not flow as freely, relationships matter more than pure performance, and the barrier to entry for angels remains high because of the domain expertise required. But that opacity creates opportunity for angels who are willing to invest time in building authentic relationships with institutional investors.
The framework is straightforward even if the execution takes years. Start by being genuinely helpful before asking for anything. Share deal flow selectively, offer domain expertise, and create content that demonstrates your thinking. Once you have established initial relationships, focus on adding value consistently through reciprocal deal sharing, diligence support, and portfolio help. Structure your co-investments to make life easy for institutional leads and avoid creating unnecessary complexity. Be ruthless about walking away from relationships that are one-sided or involve VCs who do not treat founders well. And most importantly, play the long game by maintaining relationships even when there is no immediate deal opportunity.
The result is a compounding advantage that grows more valuable over time. You get access to better deal flow because VCs share opportunities with people they trust. You get better diligence support because you can tap into institutional expertise. You get higher ownership in winning companies because you are getting into deals earlier. And you build a reputation in the market that opens doors to even more opportunities.
For angels and syndicates serious about healthcare investing, cultivating VC relationships should be treated as infrastructure investment rather than as an occasional tactic. The relationships you build in the next two years will determine what deals you see in years five through ten. That makes it one of the highest leverage activities you can invest time in, even if the payoff is not immediately obvious. The healthcare venture ecosystem rewards long-term thinking and patient relationship building. Angels who embrace that reality will build portfolios and networks that compound for decades while those chasing short-term wins will find themselves perpetually on the outside looking in.
If you are interested in joining my generalist healthcare angel syndicate, reach out to treyrawles@gmail.com or send me a DM. We don’t take a carry and defer annual fees for six months so investors can decide if they see value before joining officially. Accredited investors only.
